Evaluations of the sustainability of the viticulture associated with wine production are still scarce in the literature. Usually, the ‘carbon footprint’ assumes the environmental dimension, while the economic pillar is focused on market orientation. In the present work, the integration of both was tested using a case study supported in a six-year series (2015–2021) of primary data from a farm in the Região Demarcada do Douro (Douro Demarcated Region, hereafter the RDD). Economic and environmental inputs and outputs were collected from ‘pruning to harvest’. Profitability was calculated based on the market prices and environmental impacts using the AgriBalyse database, which is available in OpenLCA 1.10.3. In the scope of the economic results, the following costs stand out: (1) ‘human labor’; (2) use of machinery; and (3) plant protection products. Concerning the environmental impacts, the greatest weight resulted from the use of fuels, and no relation was found between the grape production variation and environmental factor variation. The indicators studied were considered valuable for comparing production systems (conventional, organic, and biodynamic, among others) and might support stakeholders’ decision making. We highlight the importance of replication in further studies to better understand the complex world of viticulture’s sustainability.